Objective

To synthesize a Ugi Product following the EXPLAN005 with phenanthrene-9-carboxaldehyde, cyclohexylamine, mandelic acid and t-butyl isocyanide. The compound will contribute towards a library for Falcipain2 inhibitors.
This compounds was ranked 49 in the DEXP014-V1B file from D-EXP014 . The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this summary post.

Procedure

As described in Explan005
This reaction used Phenanthrene-9-carboxaldehyde, cyclohexylamine, t-butylisocyanide and Furoic acid.
Phenanthrene-9-Carboxaldehyde (solid from Sigma-Aldrich)
HNMR

ID/ Lib Rank	Solvent	Aldehyde	Amine	Carboxylic Acid	Isocyanide	Ppt Yes/No
183/49	Methanol	Phenanthrene-9- carboxaldehyde	cyclohexylamine	Mandelic acid	t-butylisocyanide	Reagents Insoluble
Quantity	1000uL	0.5mmol, 103.1mg	0.5mmol, 57.2uL (density=0.867g/ml)	0.5mmol, 76.075 mg	0.5mmol, 56.5uL (density=0.735g/ml)

Density information found on the Ugi Chemicals Page in Left Navigation Bar.

Results

Photos taken directly after all the components were charged and vortexed.

183A

Discussion

Conclusion

The starting materials are insoluble.

Log

2008-04-16

15:12- Charged a vial with 1000 ul of methanol.
15:14- Weighed out the Phenanthrene-9-carboxaldehyde.
15:18- Added the cyclohexylamine to the vial.
15:19- Vortexed vial 15 seconds.
15:22- Added the phenanthrene-9-carboxaldehyde.
15:23- Vortexed vial 2 min. No clear solution was obtained.
15:27- Added the mandelic acid.
15:30- Vortexed vial 3 min. No clear solution was obtained.
15:34- Added the t-butyl isocyanide.
15:36- Vortexed 5 min. No clear solution was obtained.
15:44- A photo was taken (183A).

Exp183